4-(6-Aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid

Base Information

• Chemical Name: 4-(6-Aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid
• CAS No.: 19234-66-3
• Molecular Formula: C13H15 N5 O5
• Molecular Weight: 321.293
• NSC Number: 143678
• DSSTox Substance ID: DTXSID80301486
• Mol file: 19234-66-3.mol

Synonyms:19234-66-3;2',3'-Isopropylidene Adenosine-5'-carboxylic Acid;4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid;2',3'-O-ISOPROPYLIDENE-ADENOSINE-5'-CARBOXYLIC ACID;Isopropylidene-adenosine-5-carboxylic acid;NSC143678;9-[2,3-o-(1-methylethylidene)pentofuranuronosyl]-9h-purin-6-amine;SCHEMBL20580185;DTXSID80301486;BCP33912;AKOS030254393;NSC-143678;METHYL2-ISOCYANO-3-METHYLBUTYRATE;BS-21983;FT-0670501;SR-01000219814;J-012434;SR-01000219814-1;6-(6-amino-9h-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (non-preferred name)

Chemical Property of 4-(6-Aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid

Chemical Property:

• Melting Point: 276-279°C
• Boiling Point: 628.9 °C at 760 mmHg
• Flash Point: 334.1 °C
• PSA: 134.61000
• Density: 1.92 g/cm³
• LogP: 0.49180
• Storage Temp.: -20°C Freezer
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 321.10731860
• Heavy Atom Count: 23
• Complexity: 505

Purity/Quality:

98%,99%, ^*data from raw suppliers

2’,3’-IsopropylideneAdenosine-5’-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(O1)C(OC2C(=O)O)N3C=NC4=C(N=CN=C43)N)C
• Uses: 2',3'-Isopropylidene Adenosine-5'-carboxylic Acid is used in the preparation of nucleosides as adenosine A3 receptor agonists.

Technology Process of 4-(6-Aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid

There total 6 articles about 4-(6-Aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2',3'-isopropylidene adenosine (362-75-4) → 2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4039(00)74197-9

Reference yield:

adenosine (58-61-7) → 2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature

2: 86 percent / KMnO₄, KOH / H₂O / 24 h / Ambient temperature

With potassium hydroxide; potassium permanganate; toluene-4-sulfonic acid; In water; acetone;

DOI:10.1016/0040-4039(96)00092-5

Reference yield:

(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester (159647-45-7) → 2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3)

Guidance literature:

With triethylamine; In chloroform; water; at 25 ℃; hydrolysis, rate accelerations in the presence of several additives, addition of a carbazole derivative;

upstream raw materials:

2',3'-isopropylidene adenosine

(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester

adenosine

5'-(O-tert-butyldimethylsilyl)adenosine

Downstream raw materials:

adenosine-5'-(N-phenylcarboxamide)

2',3'-O-isopropylideneadenosine-5'-carboxylic acid methyl ester

3-({2,2-dimethyl-6-[6-(3-phenyl-ureido)-purin-9-yl]-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl}-amino)-benzoic acid methyl ester

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((S)-1-hydroxyethyl)tetrahydrofuran-3,4-diol

Refernces

• 1、 Harper,Hampton. "Conversion of 2',3'-O-isopropylidene adenosine into its 5',5'-di-C-methyl derivative.". . p. 1688 - 1689. Retrieved 1970.
• 2、 Bockman, Matthew R.,Engelhart, Curtis A.,Dawadi, Surendra,Larson, Peter,Tiwari, Divya,Ferguson, David M.,Schnappinger, Dirk,Aldrich, Courtney C.. "Avoiding Antibiotic Inactivation in Mycobacterium tuberculosis by Rv3406 through Strategic Nucleoside Modification". . p. 1102 - 1113. Retrieved 2018.
• 3、 Schmidt,Schloz,Schwille. "Synthesis of 5'-modified adenosine derivatives". . p. 590 - 594. Retrieved 1968.
• 4、 Dyba, Marcin,Da Silva, Brandon,Coia, Heidi,Hou, Yanqi,Noguchi, Sumire,Pan, Jishen,Berry, Deborah,Creswell, Karen,Krzeminski, Jacek,Desai, Dhimant,Amin, Shantu,Yang, David,Chung, Fung-Lung. "Monoclonal Antibodies for the Detection of a Specific Cyclic DNA Adduct Derived from ω-6 Polyunsaturated Fatty Acids". . p. 772 - 783. Retrieved 2018.
• 5、 -. "Biomarkers for Carcinogenesis and Uses Thereof". Paragraph 0022; 0085. . Retrieved 2019/08/02.